The 2,3-dihydroxypropylnucleoside analogues were first prepared by Ueda et al. (1971). Soon thereafter it was shown that phosphate-linked oligomers of the analogues do in fact exhibit hypochromicity in the presence of RNA and DNA in solution (Seita et al. 1972). The preparation of the polymers was later described by Cook et al. (1995, 1999) and Acevedo and Andrews (1996). The GNA-GNA self-pairing described by Zhang and Meggers is however novel, and the specificity of interaction well-demonstrated.
DNA and RNA have a deoxyribose and ribose sugar backbone, respectively, whereas GNA's backbone is composed of repeating glycol units linked by phosphodiester bonds. The glycol unit has just three carbon atoms and still shows Watson-Crick base pairing. Interestingly, the Watson-Crick base pairing is much more stable in GNA than its natural counterparts DNA and RNA as it requires a high temperature to melt a duplex of GNA. It is possibly the simplest of the nucleic acids, so making it a hypothetical precursor to RNA.
Seita, Tooru; Yamauchi, Kiyoshi; Kinoshita, Masayoshi; Imoto, Minoru. Condensation polymerization of nucleotide analogues. Die Makromolekulare Chemie (1972), 154:255-261.
Ueda, Nasuo; Kawabata, Toshio; Takemoto, Kiichi. Synthesis of N-(2,3-dihydroxypropyl) derivatives of nucleic bases. Journal of Heterocyclic Chemistry (1971), 8(5), 827-9.
Acevedo, Oscar L.; Andrews, Robert S. Synthesis of propane-2,3-diol combinatorial monomers. Tetrahedron Letters (1996), 37(23), 3931-3934.
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Cook, Phillip Dan; Acevedo, Oscar L.; Davis, Peter W.; Ecker, David J.; Hebert, Normand. Preparation of ethylene glycol phosphate linked oligodeoxyribonucleotides as phospholipase A2 inhibitors. U.S. (1999), 39 pp., Cont.-in-part of U.S. Ser. No. 179,970. CODEN: USXXAM US 5886177 A 19990323 CAN 130:237811 AN 1999:205354